Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 44, 2014 - Issue 4
315
Views
12
CrossRef citations to date
0
Altmetric
Research Article

In vitro metabolism of monensin A: microbial and human liver microsomes models

, , , , , , , & show all
Pages 326-335 | Received 15 Aug 2013, Accepted 13 Sep 2013, Published online: 17 Oct 2013

References

  • Asha S, Vidyavathi M. (2009). Cunninghamella – a microbial model for drug metabolism studies – a review. Biotechnol Adv 27:16–29
  • Asha S, Vidyavathi M. (2010). Role human liver microsomes in vitro metabolism of drugs -- a review. Appl Biochem Biotechnol 160:1699–722
  • Barth T, Conti R, Pupo MT, et al. (2012). Chiral HPLC analysis of donepezil, 5-O-desmethyl donepezil and 6-O-desmethyl donepezil in culture medium: application to fungal biotransformation studies. Anal Bioanal Chem 404:257–66
  • Bocato MZ, Pupo MT, Simões RA, et al. (2012). Solid phase microextraction and LC-MS/MS for the determination of paliperidone after stereoselective fungal biotransformation of risperidone. Anal Chim Acta 742:80–9
  • Borges WS, Borges KB, Bonato PS, et al. (2009a). Endophytic fungi: natural products, enzymes and biotransformation. Curr Org Chem 13:1137–63
  • Borges KB, Borges WS, Duran-Patron R, et al. (2009b). Stereoselective biotransformations using fungi as biocatalysts. Tetrahedron Asymmetry 20:385–97
  • Caldeira C, Neves WS, Cary PM, et al. (2001). Rhabdomyolysis, acute renal failure, and death after monensin ingestion. Am J Kidney Dis 38:1108–12
  • Capel CS, Souza ACD, Carvalho TC, et al. (2011). Biotransformation using Mucor rouxii for the production of oleanolic acid derivatives and their antimicrobial activity against oral pathogens. J Ind Microbiol Biotechnol 38:1493–8
  • Carrao DB, Borges KB, Barth T, et al. (2011). Capillary electrophoresis and hollow fiber liquid-phase microextraction for the enantioselective determination of albendazole sulfoxide after biotransformation of albendazole by an endophytic fungus. Electrophor 32:2746–56
  • Davison KL. (1984). Monensin absorption and metabolism in calves and chickens. J Agric Food Chem 32:1273–7
  • Donoho AL, Manthey JA, Occolowits JL, Zornes LL. (1978). Metabolism of monensin in the steer and rat. J Agric Food Chem 26:1090–5
  • Duax WL, Smith CD, Strong PD. (1980). Complexation of metal ions by monensin. Crystal and molecular structure of hydrated and anhydrous crystal forms of sodium monensin. J Am Chem Soc 102:6725–9
  • Faber K. (2011). Biotransfomations in organic chemistry. Berlin, Germany: Springer
  • Fortes, SS, Barth T, Furtado NAJF, et al. (2013). Evaluation of dispersive liquid--liquid microextraction in the stereoselective determination of cetirizine following the fungal biotransformation of hydroxyzine and analysis by capillary electrophoresis. Talanta 116:743–52
  • Grob CA. (1969). Mechanisms and stereochemistry of heterolytic fragmentation. Angew Chem 8:535–46
  • Grob CA, Baumann W. (1955). Die 1,4-eliminierung unter fragmentierung. Helv Chim Acta 38:594–610
  • Harris JA, Russel CAL, Wilkins JP. (1998). The characterization of polyether ionophore veterinary drugs by HPLC-electrospray MS. Analyst 123:2625–8
  • Henri J, Manceau J, Sanders P, Laurentie M. (2008). Cythochrome P450-dependent metabolism of monensin in hepatic microsomes from chickens and turkeys. J Vet Pharmacol Therap 31:584–6
  • Hilario VC, Carrao DB, Barth T, et al. (2012). Assessment of the stereoselective fungal biotransformation of albendazole and its analysis by HPLC in polar organic mode. J Pharm Biomed Anal 61:100–7
  • Huczyński A. (2012). Polyether ionophores – promising bioactive molecules for cancer therapy. Biorgan Med Chem Lett 22:7002–10
  • Huczyński A, Janczak J, Lowicki D, Brzezinski B. (2012). Monensin A acid complexes as a model of electrogenic transport of sodium cation. Biochim Biophys Acta 1818:2108–19
  • Huczyński A, Ratajczak-Sitarz M, Stefańska J, et al. (2011). Reinvestigation of the structure of monensin A phenylurethane sodium salt based on X-ray crystallographic and spectroscopic studies and its activity against hospital strains of methicillin-resistant S. epidermidis and S. aureus. J Antibiot 64:249–56
  • Huczyński A, Stefańska J, Przybylski P, et al. (2008). Synthesis and antimicrobial properties of monensin A esters. Biorgan Med Chem Lett 18:2585–9
  • Kiel DE, Julian RK, Kennington AS. (1998). Electrospray ionization mass spectrometry with in-source collision-induced dissociation of monensin factors and related metabolites. Rapid Commun Mass Spectrom 12:903–10
  • Kouyoumdjian JA, Morita MPA, Sato AK, Pissolati AF. (2001). Fatal rhabdomyolysis after acute sodium monensin (Rumensin®) toxicity: case report. Arquivos de Neuropsiquiatria 59:596–8
  • Li AP. (2001). Screening for human ADME/Tox drugs properties in drug discovery. Drug Discov Today 6:357–66
  • Li AP. (2004). In vitro approaches to evaluate ADMET drug properties. Curr Top Med Chem 4:701–6
  • Liu JH, Yu BY. (2010). Biotransformation of bioactive natural products for pharmaceutical lead compounds. Curr Org Chem 14:1400–6
  • Lopes NP, Stark CBW, Gates PJ, Staunton J. (2002a). Fragmentation studies on monensin A by sequential electrospray mass spectrometry. Analyst 127:503–6
  • Lopes NP, Stark CBW, Hong H, et al. (2001). A study of the effect of pH, solvent system, cone potential and the addition of crown ethers on the formation of the monensin protonated parent ion in electrospray mass spectrometry. Analyst 126:1630–2
  • Lopes NP, Stark CBW, Hong H, et al. (2002b). Fragmentation studies on monensin A and B by accurate mass electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom 16:414–20
  • Lowici D, Huczyński A. (2013). Structure and antimicrobial properties of monensin A and its derivatives: summary of the achievements. BioMed Res Int 2013:1–14
  • Martinek T, Riddell FG, Wilson C, Weller CT. (2000). The conformation of monensin A metal complexes in solution determined by NMR spectroscopy. J Chem Soc Perkin Trans 1:35–41
  • Messiano GB, Santos RAS, Ferreira LS, et al. (2013). In vitro metabolism study of the promising anticancer agent the lignan (−)-grandisin. J Pharm Biomed Anal 72:240–4
  • Moloney M, Clarke L, O’Mahony J, et al. (2012). Determination of 20 coccidiostats in egg and avian muscle tissue using ultra high performance liquid chromatography-tandem mass spectrometry. J Chromat A 1253:94–104
  • Moreira FL, Souza GHB, Rodrigues IV, et al. (2013). A non-michaelian behavior of the in vitro metabolism of the pentacyclic triterpene alfa and beta amyrins by employing rat liver microsomes. J Pharm Biomed Anal 84:14–19
  • Nebbia AS, Ceppa L, Dacasto M, et al. (1999). Oxidative metabolism of monensin in rat liver microsomes and interactions with tiamulin and other chemotherapeutic agents: evidence for the involvement of cytochrome P-450 3A subfamily. Drug Metab Dispos 27:1039–44
  • Nebbia AS, Ceppa L, Dacasto M, et al. (2001). Oxidative monensin metabolism and cytochrome P450 3A content and functions in liver microsomes from horses, pigs, broiler, chicks, cattle and rats. J Vet Pharmacol Ther 24:399–403
  • Parshikov IA, Netrusov AI, Sutherland JB. (2012). Microbial transformation of antimalarial terpenoids. Biotechnol Adv 30:1516–23
  • Paz FAA, Gates PJ, Fowler S, et al. (2003). Sodium monensin dihydrate. Acta Cryst 59:1050–2
  • Pekala E, Kubowicz P, Lazewaska D. (2012). Cunninghamella as a microbiological model for metabolism of histamine H3 receptor antagonist 1-[3-(4-tert-Butylphenoxy)propyl]piperidine. Appl Biochem Biotechnol 168:1584–93
  • Pospíšil S, Sedmera P, Vokoun J, et al. (1987). 3-O-Demethylmonensins A and B produced by Streptomyces cinnamonensis. J Antibiot 40:555–7
  • Pospíšil S, Zima J. (1987). Biosynthesis of monensins and 3-O-demethylmonensins in Streptomyces cinnamonensis in the presence of methylation inhibitors. FEMS Microbiol Lett 44:283–7
  • Pupo MT, Borges KB, Borges WS, Bonato PS. (2008). Fungal biotransformations: a powerful tool in drug metabolism studies. In: Saikai R, Bezbaruah RL, Bora TCh, eds. Microbial biotechnology. New Delhi, India: New India Publishing Agency, 47–66
  • Raucy JL, Lasker JM. (1991). Isolation of P450 enzymes from human liver. Methods Enzymol 206:577–87
  • Rocha BA, Pupo MT, Antonucci GA, et al. (2012). Microbial transformation of the sesquiterpene lactone tagitinin C by the fungus Aspergillus terreus. J Ind Microbiol Biotechnol 39:1719–24
  • Rokka M, Peltonen K. (2006). Simultaneous determination of four coccidiostats in eggs and broiler meat: validation of an LC-MS/MS method. Food Addit Contam 23:479–8
  • Rosén J. (2001). Efficient and sensitive screening and confirmation of residues of selected polyether ionophore antibiotics in liver and eggs by liquid chromatography-electrospray tandem mass spectrometry. Analyst 126:1990–5
  • Sousa-Junior JN, Rocha BA, Assis MD, et al. (2013). Biomimetic oxidation studies of monensin A catalyzed by metalloporphyrins: identification of hydroxyl derivative product by electrospray tandem mass spectrometry. Braz J Pharmacogn 23:621--9
  • Souza AC, Machado FS, Celes MR, et al. (2005). Mitochondrial damage as an early event of monensin-induced cell injury in cultured fibroblasts L929. J Vet Med A 52:230--7
  • Sun L, Huang HH, Liu L, Zhong DF. (2004). Transformation of verapamil by Cunninghamella blakesleeana. Appl Environ Microbiol 70:2722–7
  • Vaufrey F, Delort D, Jeminet G, Dauphin G. (1990). Bioconversion of monensin by a soil bacterium Sebekia benihana. J Antibiot 9:1189–91
  • Verza M, Arakawa NS, Lopes NP, et al. (2009). Biotransformation of a tetrahydrofuran lignan by the endophytic fungus Phomopsis sp. J Braz Chem Soc 20:195–200
  • Wharton PS, Hiegel GA. (1965). Fragmentation of 1,10-decalindiol monotosylates. J Org Chem 30:3254–7
  • Wu H, Li L, Shen J, et al. (2012). In vitro metabolism of cyadox in rat, chicken and swine using ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry. J Pharm Biomed Anal 67:175–85

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.